AU2002367745B2 - Biodegradable non-toxic gear oil - Google Patents
Biodegradable non-toxic gear oil Download PDFInfo
- Publication number
- AU2002367745B2 AU2002367745B2 AU2002367745A AU2002367745A AU2002367745B2 AU 2002367745 B2 AU2002367745 B2 AU 2002367745B2 AU 2002367745 A AU2002367745 A AU 2002367745A AU 2002367745 A AU2002367745 A AU 2002367745A AU 2002367745 B2 AU2002367745 B2 AU 2002367745B2
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- Australia
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- acids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000012208 gear oil Substances 0.000 title description 12
- 231100000252 nontoxic Toxicity 0.000 title description 5
- 230000003000 nontoxic effect Effects 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 150000007513 acids Chemical class 0.000 claims description 18
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- -1 alcohol ester Chemical class 0.000 claims description 9
- 239000000314 lubricant Substances 0.000 claims description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 9
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 8
- 229960002317 succinimide Drugs 0.000 claims description 8
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 230000003078 antioxidant effect Effects 0.000 claims description 6
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 6
- 239000012990 dithiocarbamate Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 239000007866 anti-wear additive Substances 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 239000001384 succinic acid Substances 0.000 claims description 3
- 239000005069 Extreme pressure additive Substances 0.000 claims description 2
- 239000003350 kerosene Substances 0.000 claims description 2
- 239000010687 lubricating oil Substances 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 150000001448 anilines Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 150000002462 imidazolines Chemical class 0.000 claims 2
- 239000002131 composite material Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- GGQRKYMKYMRZTF-UHFFFAOYSA-N 2,2,3,3-tetrakis(prop-1-enyl)butanedioic acid Chemical compound CC=CC(C=CC)(C(O)=O)C(C=CC)(C=CC)C(O)=O GGQRKYMKYMRZTF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000277275 Oncorhynchus mykiss Species 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 101150037603 cst-1 gene Proteins 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000003879 lubricant additive Substances 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000013535 sea water Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- TXZAMAPJUWLUGX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO.OCC(CO)(CO)COCC(CO)(CO)CO TXZAMAPJUWLUGX-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- WPUKZOKYKHYASK-UHFFFAOYSA-N bis(11-methyldodecyl) hexanedioate Chemical compound CC(C)CCCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCCCC(C)C WPUKZOKYKHYASK-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PDEDQSAFHNADLV-UHFFFAOYSA-M potassium;disodium;dinitrate;nitrite Chemical compound [Na+].[Na+].[K+].[O-]N=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PDEDQSAFHNADLV-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/126—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/127—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids polycarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/288—Partial esters containing free carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/301—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
- C10M2215/224—Imidazoles
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/081—Biodegradable compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
WO 03/087277 PCT/US02/32191 I BIODEGRADABLE NON-TOXIC GEAR OIL FIELD OF INVENTION [0001] The present invention relates to lubricant compositions and more particularly to biodegradable lubricants compositions especially useful as gear oils.
BACKGROUND OF INVENTION 100021 Commercially available lubricant compositions are prepared from a variety of natural and synthetic base stocks combined with various additive packages and solvents depending upon their intended application.
[0003] For lubricant applications requiring biodegradability of the lubricant base stock natural and synthetic ester base stocks have been extensively investigated. As might be expected no one ester will meet all of the major criteria specified for biodegradable lubricants. For example, one natural ester base stock in current use today is rapeseed oil which has very good biodegradability but poor low temperature properties and stability thus limiting its usefulness. An example of synthetic ester basestocks in current use are neopolyol esters formed by the esterification of neopolyols with mono- or dicarboxylic acids. For a given combination ofneopolyol(s) and acid or acids there is a set of product properties that includes those such as viscosity, viscosity index, molecular weight, pour point, stability, demulsibility, and biodegradability, to mention just a few.
100041 In those applications requiring biodegradable base stocks often it is also required that the lubricant additive employed with the base stock be WO 03/087277 PCT/US02/32191 -2substantially non-toxic. This is especially true if the lubricant composition is used on or near water or where it could possibly leak into the soil. Unfortunately many lubricant additives have poor environmental characteristics.
(0005] Experience has shown that most environmental type, gear oils are either biodegradable and non-toxic with poor performance in terms of gear protection and oil life, or they have good functional performance but lack the desired environmental characteristics. Thus, there is a need for a gear oil composition that has improved functional performances while maintaining low aquatic toxicity and biodegradability.
10006] Accordingly, one object of the present invention is to provide improvements in gear performance of biodegradable non-toxic gear oils.
10007] Another object of the present invention is to provide a gear oil composition that has balanced performance such as, for example, good rust inhibition without comprising FZG scuffing test performance.
10008] These and other objects of the invention will become apparent from the description set forth below.
SUMMARY OF INVENTION 10009] A biodegradable lubricating oil composition comprising: a major amount of a synthetic alcohol ester basestock formed by from the reaction product of: mono- and dipentaerythritol and mixed acids comprising about 2 to mole linear mono carboxylic acids having from about 5 to about 12 WO 03/087277 PCT/US02/32191 -3carbon atoms, about 30 to about 70 wt%/ of a branched mono carboxylic acid having from about 15 to about 20 carbon atoms and from about 20 to about 30 mole of a dicarboxylic acid or anhydride of a dicarboxylic acid having from about 4 to about 8 carbon atoms wherein the basestock has a viscosity at 100 0 C in the range of about 20 to about 50 cSt at 100°C and a pour point of less than about -20°C; and an effective amount of a polyoxyalkylene alcohol demulsifying agent, a combination of alkylated organic acid and ester thereof and ashless succinimide rust inhibitors and an ashless dithiocarbamate antiwear and extreme pressure agent.
DETAILED DESCRIPTION OF THE INVENTION [0010] The synthetic alcohol ester basestock used in the gear oils of the present invention is preferably formed from the reaction of mono- and dipentaerythritol and mixed acids. Typically the mole ratio of mono- to dipentaerthritol used is in the range of 80:20 to about 99.9:0.1.
[0011] The mixed acids employed in forming the esters comprises about 2 to mole linear mono carboxylic acids having from about 5 to about 12 carbon atoms, about 30 to about 70 wt% of a branched mono carboxylic acid having from about 10 to about 25 carbon atoms, preferably 15 to about 20 carbon atoms and from about 20 to about 30 mole of a dicarboxylic acid having from about 4 to about 8 carbon atoms.
10012] The synthetic esters are formed by reacting the mono- and dipentaerithritol with the mixed acids under conventional esterification conditions well WO 03/087277 PCT/US02/32191 -4known in the art. See for example, the Encyclopedia of Chemical Technology, Fourth Edition, Volume 9, pages 755-812 and the references cited therein.
[0013] The esters used in the compositions of the invention will have a viscosity in the range of about 20 to about 50 cSt at 100 0 C and a pour point of less than about -35 0
C.
[0014] In an alternate embodiment a blend of esters formed as set forth above may also be used in formulation the gear oils of the invention.
[0015] Indeed in one embodiment two esters are used. One is the reaction product of mono- and dipentaerythritol and mixed acids comprising 30 to mole of C 7 to C 10 linear acids, from 24 to 28% of a dicarboxylic acid having 5 to 7 carbon atoms and from 34 to 40 mole of a branched acid having 17 to 19 carbon atoms. The other is the reaction product of(l) above and (2) mixed acids comprising 2 to 6 mole of C 7 to C 10 linear acids, form 25 to 29 mole of a dicarboxylic acid and from 65 to 70 mole of a branched acid having 17 to 19 carbon atoms.
[0016] The lubricant compositions of the invention are formed by blending the ester base stock together with at least an effective amount of a polyoxyalkylene alcohol demulsifying agent, an ashless dithiocarbamate antiwear and extreme pressure agent, and a combination of alkylated organic acid and ester thereof and ashless succinimide rust inhibitors.
[0017] A suitable polyoxyalkylene alcohol demulsifying agent is characterized by the formula WO 03/087277 PCT/US02/32191
OH
where EO is ethylene oxide moiety and PO is propylene oxide moiety, x and y represent the relative amounts of each. A preferred demulsifying agent will have a MW in the range of about 1700 to 3000 and an EO/PO ratio of from about 20/80 to about 1/99. Typically the polyoxyalkene alcohol demulsifying agent is dissolved in a solvent such as tricrylphosphate (TCP). Especially useful is a solution comprising from about 85 to 95 wt% TCP.
[0018] A suitable ashless dithiocarbamate antiwar and extreme pressure is characterized by the formula S S S1 II R/ R2 Ri' where R 1 and R 2 may be the same or different alkyl groups of from 1 to about 12 carbon atoms and preferably R 1 and R 2 are the same and have four carbon atoms.
[0019] Among suitable alkylated organic acids and esters thereof specific mention is made of alkylated succinic acid and esters thereof and especially tetra propenyl succinic acid and the monoester thereof where R is the monoester moiety, -COOR, is a C 1 to C 4 hydrocarbyl group. A mixture of about 70 wt%/ of the tetrapropenyl succinic acid and less than about 30 wt%/ of the ester is available as LZ 859 from Lubrizol Corporation, Wickliffe, Ohio.
WO 03/087277 PCT/US02/32191 -6- [0020] Among suitable ashless succinimides known in the art specific mention is made of the reaction product of tetrapropenyl succinic anhydride and the intermediate product of oleic acid with triethyl amine. Such ashless succinimides are sold under the trade name Hitec 537 by Ethyl Corp., Richmond, Virginia and under the trade name RT70B by ExxonMobil Chemical Company, Houston, Texas.
[0021] The composition of the invention may include other optional additives.
[0022] Preferably the additives listed in Table 1 are used in amounts sufficient to provide the normal function. Typical amounts for individual components are also set forth in the table. The balanced performance is achieved by carefully selecting the additives in the proper proportions to attain all of the necessary performance objectives.
TABLE 1 (Broad) wt%/ (Preferred) wt% Ashless dithiocarbamate in TCP 0.3-2.5 1.0-1.4 antiwear/extreme pressure additive Metal passivator or N,S-heterocyclic) 0.05-0.20 0.08-0.15 Demulsifying agent (polyoxyalkylene 0.03-0.30 0.05-0.18 alcohol in TCP solvent) Antirust agents (one or more: imidazoline, 0.03-0.35 0.10-.25 succinic acid half ester, succinimide) Ashless phosphorus antiwear agents 0.20-2.5 0.30-1.00 Antioxidant(s) 0.10-0.50 0.15-0.20 Defoamant concentrate 0.10-1.00 0.35-0.70 Base stock 90% WO 03/087277 PCT/US02/32191 -7- EXAMPLE 1 [0023] A synthetic alcohol ester was prepared by esterifying a pentaerythritol composition and a mixed acid composition at 212 to 218 0 C until TAN The pentaerythritol and acid compositions are given in Table 2.
[0024] When TAN 0.5 was reached the reaction mixture was stripped at 212-218 0 C/10 mm Hg. The remaining product was treated with activated charcoal and water and then stripped at 95 0 C/10-20 mm Hg for 1 to 2 hours.
[0025] The product had the properties shown in Table 3.
EXAMPLE 2 [0026] The procedure of Example 1 was followed using the acids and alcohols shown in Table 2.
[0027] The product had the properties shown in Table 3.
TABLE 2 Acid Composition, approximate mole nC 7 nCg Adipic acid Isostearic acid Alcohol composition, mole monopentaerythritol dipentaerythritol Example 1 19% 11% 8% 25% 37% 99.3% .7% Example 2 2% 1% 1% 27% 69% 91% 9% WO 03/087277 WO 03/87277PCT/JS02/32191 8- TABLE 3 Physical Properties Viscosity at 100"C Viscosity at 40*C
TAN
Pour Point, 0
C
Example 1 26.6 cSt 270 cSt 1 -33 Example 2 42.8 cSt 488 cSt 1 -24 COMPARATIVE EXAMPLE 3 [00281 A series of gear oils were formulated having the compositions shown in Table 4.
TABLE 4
W/O
A B C Extreme Pressure Sulfurized isobutylene 1.38 1L40 1.40 Antiwear Amine phosphate! 0.58 0.60 0.60 complex Metal N-heterocycle 0.12 0.15 0.15 passivator/antiwear Metal passivator N- or N,S-heterocycle 0.05 0.05 0.05 Antioxidant Hindered phenol and/or 0.50 0.50 1.50 aromatic amine Demulsifier Polyoxyalkylene alcohol in 0.10 TCP solvent____ Defoamant polysiloxane and/or 0.10 0.50 0.50 concentrate polyacrylate in kerosene Base stock Example 2 97.22 96.65 95.75 TOTAL 100 100 100 WO 03/087277 WO 03/87277PCT/JS02/32191 -9- EXAMPLE 3 100291 A series of gear oils were formulated having the compositions shown in Table TABLE Component Function Antiwear/EP Demulsifier Rust inhibitor Rust inhibitor Antiwear Antioxidant(s)/ metal passivator(s)/ defoamant Base stock Base stock Base stock Chemical Type ashless ditbiocarbamate Polyoxyalkylene alcohol in TCP solvent Ashless succinimide Ashless alkylated succinic acid and esters thereof Phosphorus anti-wear additives Various Di-isotridecyl adipate Example I Example 2
D
1.2 .15 .10 .10 0.75 0.76 93.94
W/O
E
1.2 .15 .10 .10 0.75 0.76
F
1.2 0.75 0.76 53.47 43.47 96.94 COMPARATIVE EXAMPLE 4 [00301 The performance characteristics for the formulations A, B and C of Comparative Example 3 were measured and are given in Table 6.
TABLE 6 Properties Biodegradability Aquatic toxicity KV 40-C (D445-3) KV 100-C (D445-5) Copper corrosion, ASTM D130,24 hours 121TC Pour Point, 'C ASTM Rust, distilled water/synthetic sea water Bethlehem Steel Rust, A/B/C Demulsibility (D1401) time to 37 ml water FZG scuffing fail stage Requirements 80% minimum in CEC L-33 LL50 1000 ppm in rainbow trout test Results A B C 96 1,184 147.9 18.25 434.1 37.26 4A 417.5 35.86 4C 2B maximum -30O maximum pass/pass pass/pass/pass 10 typical 12 minimum 350 pass/pass pass/pass/fail (severe) 60 typical 13+ pass/pass pass/pass/fail (severe) typical 13 pass/pass pass/pass/pass 13+ WO 03/087277 PCT/US02/32191 11 EXAMPLE 4 [0031] The performance characteristics for the formulations D, E and F of Example 3 were measured and are given in Table 7.
[0032] As can be seen, compositions A, B and C of Table 4 meet some, but not all of the requirements for commercially acceptable gear oils. The biodegradability and aquatic toxicity for those oils are acceptable. The oils also meet the FZG Scuffing Test requirement, but they fail to meet the rust and corrosion requirements needed to protect gears and bearings, especially those operating in potentially wet environments. The compositions D, E and F of Table 5 meet all of the requirements, including biodegradation, aquatic toxicity and FZG Scuffing Test, as well as copper corrosion protection and rust inhibition.
TABLE 7 Properties Biodegradability Aquatic toxicity Requirements 80% minimum in CEC L-33 LLSO 1000 ppm in rainbow trout test
D
87 Results
E
90
F
92 1898 227.8 23.36 KV 40 0 C (D445-3) KV 1 00-C (D445-5) Copper corrosion, ASTM D 130, 24 hours@ 121 *C Pour Point, 'C ASTM (D3665) rust distilled water/synthetic sea water Bethlehem Steel Rust, AIB/C Demulsibility (D1401) time to 37 ml water FZG scuffing fail stage 3185 322.2 30.18 2A -33 pass/pass 5013 444.6 37.53 2A pass/pass 2B maximum -30' maximum pass/pass pass/pass/pass 10 typical 13+ 2A -39 pass/pass pass/pass/pass 20 13+ pass/pass/pass to 13+ pass/pass/pass 13+
Claims (10)
1. A biodegradable lubricating oil composition comprising: a major amount of one or more biodegradable synthetic alcohol ester basestocks formed from the reaction product of: mono- and dipentaerythritol and mixed acids comprising about 2 to mole linear monocarboxylic acids having from about 5 to about 12 carbon atoms, about 30 to about 70 wt% of a branched monocarboxylic acid having from about 15 to about 20 carbon atoms and from about 20 to about 30 mole of a dicarboxylic acid having from about 4 to about 8 carbon atoms wherein the basestock has a viscosity at 100°C in the range of about 20 to about 50 cSt at 100 0 C and a pour point of less than about 0 C; and an effective amount of a polyoxyalkylene alcohol demulsifying agent, an ashless dithiocarbamate antiwear and extreme pressure agent, and a combination of alkylated organic acids and esters thereof and ashless succinimide rust inhibitors.
2. The composition of claim 1 wherein the demulsifying agent is a solution having from about 85 to 95 wt% solvent and the solution of demuslify- ing agent is from 0.03 to .30 wt%/ of the composition, the combination of rust inhibitors is from 0.03 to 0.35 wt% and the antiwear and extreme pressure agent is from 0.3 to 2.5 wt% of the composition.
3. The composition of claim 2 wherein the mixed acid comprise to 40 mole of C 7 to C 10 linear acid, from 24 to 28 0 C of a dicarboxylic acid WO 03/087277 PCT/US02/32191 14 having 5 to 7 carbon atoms and from 34 to 40 mole of a branched acid having 17 to 19 carbon atoms.
4. The composition of claim 2 wherein the mixed acids comprise 2 to 6 mole of C 7 to C 10 linear acids, from 25 to 29 mole of a dicarboxylic acid and from 65 to 70 mole of a branched acid having 17 to 19 carbon atoms.
The composite of claim 3 including a second alcohol ester formed from the reaction product of mono- and dipentaerythritol and (ii) mixed acids comprising 2 to 6 mole of C 7 to C 10 linear acids from 25 to 29 mole of a dicarboxylic acid and from 65 to 70 mole of a branched acid having 17 to 19 carbon atoms.
6. The composition of claims 1 to 4 wherein the ratio of mono- to dipentaerythritol is in the range of 80:20 to 99.9:0.1.
7. The composition of claim 2 wherein the composition includes a rust inhibitor, metal passivator, antifoamant, extreme pressure additive, antiwear additive and antioxidant.
8. The composition of claim 7 wherein, based on the totalweight of the composition, the rust inhibitors are present in an amount of from 0.03 to 0.30 wt% and is selected from the group consisting of imidazolines, succinic acid half esters, succinimide and mixtures thereof, (ii) the metal passivator is present in ani amount of form 0.05 to 0.20 wt% and is selected from the group consisting of N and N and S heterocyclic metal passivators, (iii) the antioxidant is a mixture of phenyl amines and tolyltriazoles and is present in an amount of from 0.10 to 0.50 wt%, and (iv) the antifoamant is selected from polysiloxanes and polyacrylates in kerosene solvent and is present from 0.10 to 1.0 wt%. WO 03/087277 PCT/US02/32191 15
9. A lubricant composition comprising: greater than 90 wt%/ based on the total weight of the composition of a synthetic ester basestock having a viscosity at 100°C in the range of about 2 to 50 cSt and a pour point of less than -30 0 C; and formed from the reaction product of(l) mono- and dipentaerythritol and (2) mixed acids comprising 30 to 40 mole of C 7 to C 1 0 linear acid, from 24 to 28% of a dicarboxylic acid having 5 to 7 carbon atoms and from 34 to 40 mole of a branched acid having 17 to 19 carbon atoms; (ii) the reaction product of mono- and dipentaerythritol and (2) mixed acids comprising 2 to 6 mole of C 7 to C 10 linear acids, from 25 to 29 mole of a dicarboxylic acid and from 65 to 70 mole of a branched acid having 17 to 19 carbon atoms; and based on the total weight of the composition from 0.03 to 0.30 wt of a polyoxyalkylene alcohol demulsifier solution having from 85.to 95 wt/o TCP, and from 0.3 to 2.5 wt%/ of an ashless dithiocarbamate antiwear and extreme pressure agent, from 0.03 to 0.35 wt%/ of a combination of alkylated organic acid and esters thereof and ashless succinimide rust inhibitors. The composition of claim 9 wherein, based on the total weight of the composition, the rust inhibitor is present in an amount of from 0.03 to 0.30 wt% and is selected from the group consisting of imidazolines, succinic acid half esters, succinimide and mixtures thereof, (ii) the metal passivator is present in an amount of form 0.05 to 0.20 wt/ and is selected from the group WO 03/087277 PCTIUS02/32191 16 consisting of N and N and S heterocyclic metal passivators, (iii) the antioxidant is a mixture of phenyl amines and tolyltriazoles and is present in an amount of firom 0.
10 to 0. 50 and (iv) the antifoamant is selected from polysiloxanes and polyacrylates and is present from 0. 10 to 1. 0 wt 0 /o.
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| US60/328,321 | 2001-10-10 | ||
| US10/266,385 US6649574B2 (en) | 2001-10-10 | 2002-10-08 | Biodegradable non-toxic gear oil |
| US10/266,385 | 2002-10-08 | ||
| PCT/US2002/032191 WO2003087277A2 (en) | 2001-10-10 | 2002-10-08 | Biodegradable non-toxic gear oil |
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| AU2002367745B2 true AU2002367745B2 (en) | 2007-05-10 |
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-
2002
- 2002-10-08 CA CA2463308A patent/CA2463308C/en not_active Expired - Fee Related
- 2002-10-08 US US10/266,385 patent/US6649574B2/en not_active Expired - Lifetime
- 2002-10-08 EP EP02807242A patent/EP1434836B1/en not_active Expired - Lifetime
- 2002-10-08 AU AU2002367745A patent/AU2002367745B2/en not_active Ceased
- 2002-10-08 WO PCT/US2002/032191 patent/WO2003087277A2/en active IP Right Grant
- 2002-10-08 BR BR0213159-5A patent/BR0213159A/en not_active Application Discontinuation
- 2002-10-08 JP JP2003584221A patent/JP4423047B2/en not_active Expired - Fee Related
-
2004
- 2004-04-20 NO NO20041629A patent/NO20041629L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US6649574B2 (en) | 2003-11-18 |
| EP1434836A4 (en) | 2005-01-19 |
| NO20041629L (en) | 2004-04-20 |
| US20030125218A1 (en) | 2003-07-03 |
| EP1434836B1 (en) | 2013-01-16 |
| CA2463308C (en) | 2010-12-14 |
| WO2003087277A3 (en) | 2004-04-08 |
| AU2002367745A1 (en) | 2003-10-27 |
| JP4423047B2 (en) | 2010-03-03 |
| BR0213159A (en) | 2004-09-14 |
| WO2003087277A2 (en) | 2003-10-23 |
| JP2005520038A (en) | 2005-07-07 |
| CA2463308A1 (en) | 2003-10-23 |
| EP1434836A2 (en) | 2004-07-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |